Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite
A cozy sleeping area is defined by a soft white bed adorned with decorative pillows. Warm light is provided by unique hanging fixtures. A wooden table displays an arrangement of fruits and snacks alongside elegant candle holders, creating a welcoming and intimate setting.
Tower in Pleasant Hill
4.9 out of 5 average rating, 214 reviews

Kick Cancers Ass With A Stay

Unique. For a Cause. Fun. A place where your stay truly counts! Your stay… Enjoy a night(s) away in an old grain elevator silo that now is home to a fully open concept layout with the most comfortable bed, a soaking tub of your dreams, handmade exposed copper piping & every detailed covered for the perfect getaway! The Cause… 20% of every nights stay goes to Pink Ribbon Good helping local ladies fight cancers. On Site… Coffee & Ice Cream Shop Axe Throwing Sand Volleyball Yard Games Boutiques

Superhost
A spacious living room features a light-colored sofa and two matching armchairs, designed for comfort. A dark wood coffee table sits in the center, accompanied by two cups and a decorative fruit bowl. Natural light streams through the windows, highlighting the patterned area rug.
Apartment in Old West End
4.93 out of 5 average rating, 187 reviews

Downtown Old West End-Fun central local with porch

This apt. is one of my favorite spaces. We used to live here and I think you will find it to be a relaxing and comfortable place to spend your time in Muncie. We've provided the basics so that it can be your home away from home: fully functioning kitchen, coffee options, hi speed internet, towels, shampoo, conditioner, soaps, bedding, roku with tv, and board games. 1/2 mile to shops & dining or a walk along the river, 1 mile to BSU. Close the day grilling out while you watch the gorgeous sunset.

Top guest favorite
A serene bedroom features a spacious bed with soft linens and decorative pillows. A reading chair is positioned next to large windows, allowing natural light to illuminate the room. A decorative sign and plants add subtle character to the calming atmosphere.
Guest suite in Muncie
4.97 out of 5 average rating, 425 reviews

The Eagles Nest, two bedroom retreat.

Peaceful, centrally-located historic 1892 Queen Anne Victorian home. The Eagle's Nest has private entrance, off street parking, 2 bedrooms, furnished suite on the 2nd floor overlooking White River. Walk 0.6 miles to downtown Muncie, less than 2 miles to Ball State Univ. and 2 blocks to the Bob Ross Experience (Minnetrista). Nearby eatery and brewery options. Just 29 steps to 62-mile Cardinal Greenway, longest trail in Indiana. Might see an eagle hunting along the river too. You will love it!

Top guest favorite
The exterior of a two-story Techbuilt home is surrounded by lush greenery, showcasing large windows that invite natural light. A mature tree stands nearby, providing shade to the well-kept yard. The cedar siding highlights the home's mid-century architectural style.
Apartment in Richmond
4.92 out of 5 average rating, 586 reviews

Private Apartment-800sq ft Next to Earlham College

Upper level separate apartment. Short stroll to Earlham College campus, ball fields, tennis courts, stables and Athletic Center. 5 houses up from the President's house. Windows galore offer natural lighting. Quiet neighborhood. Hardwood floors give that cozy feeling. Guaranteed clean and private. Well-behaved pets welcome. Breakfast not included. Coffee, tea, microwave, toaster oven and refrigerator in apartment. Host lives in lower apartment with dog and 2 cats. Chickens in the back yard.

Guest favorite
A timber-framed home is set within a lush landscape, featuring a tranquil swimming pool surrounded by vibrant shrubs and greenery. Two lounge chairs are positioned near the pool, while trees provide shade. The exterior of the home showcases a green metal roof against a clear blue sky.
Guesthouse in Eaton
4.88 out of 5 average rating, 360 reviews

Cozy Pool House in the Country on 25 acres

The pool house is close to Muncie, Indiana and Ball State and Taylor Universities. We are also only about 5 miles from Barn on Boundary and have hosted several wedding parties. You’ll love our place because of the location, it feels like a secluded lodge. The timber frame structure is unique and has all the comforts of home. It has a very open floor plan and is very quiet and peaceful. It is good for couples, solo adventurers, families (with kids), big groups, and furry friends (dogs).

Top guest favorite
Home in Greenville
4.91 out of 5 average rating, 197 reviews

18 LakeS, Dead End Lane, DogS, SpaciouS, Ice Fish

Nestled within the serene surroundings of a picturesque lake community, this delightful lake house offers a charming blend of comfort and convenience. Boasting 3 bed,2 baths, a spacious living room and large kitchen. Outdoors you'll find a dock, paddle boat,& 18 lakes to enjoy. Located as the 1st house of 3 on a quiet dead end. Perfect for those looking to enjoy peaceful evenings on the lake. We are happy to welcome dogs for a fee. 2 guest fishing passes are INCLUDED with your stay.

Top guest favorite
A spacious living room is enhanced by green walls and natural light from large windows. Comfortable seating is arranged around a rustic coffee table, with a media console displaying a television. A decorative rug adds warmth to the polished wooden floor.
Cottage in Richmond
4.95 out of 5 average rating, 515 reviews

The Cottage on Abington Pike - Earlham College

Charming private cottage (home) on the West edge of Richmond within walking distance to Earlham College. This updated Three bedroom home has one custom full bath (w/Tub) & one half bath. The kitchen has been updated and is on the lower level. Great location. Wooded private rear yard with covered patio. Cardinal Greenway, Gorge Trail all of Richmond nearby. Fast Wi-Fi. Large Living room & Game room w/Pinball & Multi-cade. Outside quiet 10:00PM. Parties not allowed. 2 Tvs.

Guest favorite
A welcoming outdoor seating area is showcased with a comfortable armchair positioned next to a small wooden dining table. Potted plants add a touch of greenery, while decorative string lights overhead create a cozy ambiance. A white fence provides privacy.
Apartment in Hagerstown
4.89 out of 5 average rating, 142 reviews

New Hagerstown Apartment-Self Check-in. Sleeps 4+

Have fun with the whole family at this stylish place. Whether you are looking to visit family in the area or just wanting a small-town vibe to escape to, my welcoming apartment has everything you need. The unit comes with AC, Wi-Fi, Netflix, a private bathroom, and a fully stocked kitchen. Located in the heart of Hagerstown, the unit is blocks away from the local shops and restaurants on Main Street. My adorable apartment offers a deck, grill, pull-out couch, Keurig, and more!

Guest favorite
The kitchen and dining area is presented with sleek hardwood flooring and bright natural light. A wooden counter with four high stools faces the kitchen, where modern appliances are visible. A dining table for six is arranged nearby, complementing the welcoming space.
Guesthouse in Muncie
4.87 out of 5 average rating, 364 reviews

Carriage House Loft Apartment

Welcome to our recently remodeled Carriage House Loft Apartment! We're happy to share our simple, comfortable, cozy space with you. Refurbished original hard wood floors with updated kitchenette area and bathroom. Charming and convenient, walk two blocks to the Cardinal Greenway & White River trails, and one mile to downtown Muncie! Perfect for 2 - 4 people, or a family with an infant/toddler. Enjoy self-check-in, privacy, & dedicated parking steps from the entrance.

Guest favorite
A wooden walkway leads to a rustic cabin and a shed, situated near a calm pond. The structure features a covered patio with seating, surrounded by greenery. Soft pastel colors fill the sky during twilight, enhancing the serene rural setting.
Cabin in Economy
4.94 out of 5 average rating, 153 reviews

"The Love Shack" Rustic Cabin Getaway

Cabin and/or camper spot, with 30 amp electric & hydrant water. Cabin has 1 full bed, bunk beds (max 4, bring your own linens, firm mattresses) equipped with AC/heat & mini fridge. Indiana's best keep secret - The Love Shack - nestled down a long lane in between 2 fields in rural Economy Indiana with pond & 3 acres to yourself. Started by my grandpa Tom Bond in 2000 and loved by all that visit. Follow us on social media. 2.5 miles to Cardinal greenway.

Top guest favorite
A well-maintained exterior view of a modest structure featuring a green roof and light-colored siding. The entrance is framed by a wooden deck with a railing, accompanied by landscaped stones and decorative elements, including small sculptures and shrubs. Natural light highlights the inviting entryway.
Farm stay in Greens Fork
4.96 out of 5 average rating, 201 reviews

A country night under the stars!

Get away from it all when you stay under the stars. Join us for a peaceful country stay, close enough to drive to nearby shopping and dining, and far enough to hear the crickets and see the stars. Your cozy place will include a kitchenette, coffee pot, microwave & TV. The dining area inside or on the attached deck, full size bed & full bath with shower. Only 3.9 miles from Interstate 70. Should you choose to use 100-foot zipline to exercise your pet.

Top guest favorite
A front porch area is visible, featuring two white wicker chairs with blue pillows positioned around a small dark table. A patterned rug lies underneath. A ceiling fan can be seen above, while greenery is present in the background, enhancing the outdoor setting.
Apartment in Greenville
4.96 out of 5 average rating, 217 reviews

Cozy one bedroom apartment in a Century old house

This first floor one bedroom apartment is in a quiet neighborhood just 4 blocks from Wayne Hospital, 5 blocks from Darke County Fairgrounds and a short 5 minute walk to Downtown Greenville. It sleep up 4. The living room has a queen size sofa bed. IT has a TV with Spectrum streaming app. WiFi is available. It has a fully equipped kitchen with coffee maker and microwave. Other features include a washer and dryer and free street parking.

Popular amenities for Winchester vacation rentals

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